methyl O-(2-O-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl O-(2-O-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 388079-33-2
• Molecular Formula: C₄₃H₅₀O₉
• Molecular Weight: 710.865
• Mol file: 388079-33-2.mol

Synonyms:methyl O-(2-O-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property of methyl O-(2-O-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O-(2-O-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

There total 7 articles about methyl O-(2-O-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 40.0%

(2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol (69850-47-1) + 2-O-allyl-3,5-di-O-benzyl-D-ribofuranose → methyl O-(2-O-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (388079-33-2) + methyl O-(2-O-allyl-3,5-di-O-benzyl-α-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Guidance literature:

With trimethylsilyl bromide; tetrabutylammomium bromide; cobalt(II) bromide; 4 A molecular sieve; In dichloromethane; at 25 ℃;

DOI:10.1246/bcsj.74.1679

Reference yield:

benzyl bromide (100-39-0) → methyl O-(2-O-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (388079-33-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 54 percent / Bu₂SnO; tetrabutylammonium bromide; molecular sieves 4A / benzene / 2 h / Heating

2: 88 percent / NaH / 2 h / 80 °C

3: 99 percent / aq. AcOH; aq. H₂SO₄ / 1 h / 80 °C

4: 40 percent / trimethylsilyl bromide; cobalt(II) bromide; tetrabutylammonium bromide / molecular sieves 4A / CH₂Cl₂ / 25 °C

With trimethylsilyl bromide; 4 A molecular sieve; sulfuric acid; tetrabutylammomium bromide; sodium hydride; di(n-butyl)tin oxide; acetic acid; cobalt(II) bromide; 4 A molecular sieve; In dichloromethane; benzene;

DOI:10.1246/bcsj.74.1679

Reference yield:

L-rhamnose (73-34-7) → methyl O-(2-O-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (388079-33-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / methanesulfonic acid / 5 h / Heating

2: 76 percent / pyridine / 16 h / 60 °C

3: 2.45 g / NaH / dimethylformamide / 1.25 h / 0 - 20 °C

4: 1.074 g / CF₃CO₂H; MeOH / CH₂Cl₂ / 1 h / 20 °C

5: 40 percent / trimethylsilyl bromide; cobalt(II) bromide; tetrabutylammonium bromide / molecular sieves 4A / CH₂Cl₂ / 25 °C

With pyridine; methanol; methanesulfonic acid; trimethylsilyl bromide; tetrabutylammomium bromide; sodium hydride; trifluoroacetic acid; cobalt(II) bromide; 4 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.74.1679

upstream raw materials:

(2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol

L-rhamnose

benzyl bromide

methyl 3,5-di-O-benzyl-α-D-ribofuranoside

Downstream raw materials:

methyl O-(3,5-di-O-benzyl-β-D-ribofuranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside